Our Lead(H)er series features impressive women leaders in the tech industry. In this Q&A, we are featuring Terry Trail, Senior Manager of PMO at Paperless Parts.
Where did you grow up and how would you describe yourself as a child?
I grew up in Nashua, New Hampshire and attended a large high school where I enjoyed all the opportunities of a big school - chorus, swim team, track team, fellow students from a wide range of backgrounds and upbringings, an expansive class selection, and an overall unique experience. I always liked to try new things, even if I was not good at them, and I think that made me resilient to stick with things later on in life.
What did you study in college and what was your first job out of school?
I earned a Bachelors of Science in Business Administration at Babson College, with a concentration in Literature and Visual Arts. At Babson I learned our number one mantra: “Think outside the box”. I started work as an Implementation Consultant and worked for seven years in that role before moving on to manage teams in Implementation and Project Management.
Can you share the details on your career path and what were the critical moments that got you to where you are today?
I have had a series of good fortune moments which became key points in my career, powered by longer periods of hard lessons, a desire to constantly improve, and thinking outside of the box. All my best roles came from connections with friends and my network of former colleagues, and the more challenging times in my career taught me how to adapt, stay positive, and learn from the people around me.
First: Friends
Starting in the role that I now manage was my first critical moment - I didn’t know that I was going to enjoy project management, but a friend of mine from Babson referred me for a job at Bullhorn, where I think I was around the 70-ish employee. I grew a lot in this role, got to travel the world, saw Bullhorn’s sale to a private equity firm, and met fantastic people there (including my husband and a few more people I’ll bring up later). After over six years at Bullhorn, I wanted to try my hand at mobile apps - they were the cool new technology and I had just gotten an iphone.
Second: Network
My next critical moment came when a former colleague from Bullhorn had a Program Manager role open at Runkeeper - the first app I downloaded from the app store!!! I gladly accepted the role in which I led development of our brand offerings, had amazing experiences with the best coworkers anyone could ask for, learned what Agile Development really was, and saw Runkeeper’s sale to ASICS.
Third: Skiing (more of a coincidence, but you’ll see what I mean)
I loved working at Runkeeper, but in 2017, my husband and I wanted to move to the mountains; it being pre-pandemic, remote work wasn’t as readily available and moving out of the city wasn’t cool yet. We left our jobs and took new roles in Vermont, where I tried my hand at Product Management in the ski and hospitality tech industry. While Product Management is really cool, I just kept wanting to project manage everything (and my friends will tell you I do this in everything in my life). A layoff sped up my search and that led a Runkeeper friend visiting for a ski weekend to refer me for a Project Manager role at ASICS, the company I had left in 2017. My latest critical moment came with another ski weekend this past winter - my friend and former Bullhorn colleague Jon Dorr came to my house in February under the guise of catching up over a beer. He immediately told me about this new start-up he was joining, Paperless Parts, and told me he wanted me to join him and build-out and manage the Project Management team. This was exactly what I wanted to get back to doing - and a combo of friends, network, and skiing (and maybe mostly my experience) aligned - I interviewed as soon as I could and started in May.
What is your current role and responsibilities?
I manage the Paperless Parts Project Management team, which guides our new clients through the process of Onboarding onto the Paperless Parts platform. My responsibilities include managing and mentoring the team, facilitating improvement of our processes, helping the Project Managers with escalations and progression of their projects, interviewing potential new PMs (We’re hiring!), collaborating across the company for client prioritization and internal processes, assigning new onboardings and monitoring progress of our in-flight onboardings, and overall being the central point of contact for all Onboardings internally and externally. I love all of it because everyone at Paperless is collaborative and genuinely nice - and our clients are pretty awesome too.
Looking back, is this where you thought you’d be professionally? Was it always your goal to be in this position?
Yes it was always my goal to be in a position of building a team and mentoring Project Managers. Had I not taken a break from managing a team to try out Product, I think I would have reached this position earlier in my career, but getting that experience was invaluable to building my awareness of Product as a function and the people that manage it. I tell this part of my story to people because I think we sometimes are too afraid to “get off our path” to try out something new. To those people I always say, “Think about what the worst case scenario is and if you want to risk that happening. Is it the possibility that you would have to leave your position and realign your career because you found it wasn’t a good fit? Is it that you might give up the really comfortable position you have now? How bad would that be for you and what would be the steps to work through that scenario? What would you learn?”. Thinking through what might happen can help you weigh that risk and maybe realize that the potential risk isn’t really that bad.
For people who are looking to be in a similar position, what advice would you give to others in terms of helping them achieve their career goals?
My advice for someone wanting to manage and build teams is to learn the position you are looking to lead inside and out, and learn how to have fun in it. You can’t lead a team if you don’t enjoy the role itself. The way I learned to enjoy Project Management is through the teammates I worked with, the places I got to travel to, and the relationships I built with clients. I can’t tell you how many times I meet up with an old coworker and we laugh SO hard at some of the good and tough times we went through together. Additionally, getting into a leadership position can be tough - you have to prove you can both do the role and have leadership potential, and you also have to hit your timing right for when your company or a new company is looking to hire for this role AND they are willing to take a risk on someone who hasn’t led before. My advice here is to communicate with your manager on your desire to be a leader, ask for direct feedback on what you need to do to get there, and actively take action on the feedback.
What are the most important skills that you need to do your job well?
Empathy. Transparency. Relationships.
Empathy - Appreciate where your teammates and clients are coming from and show them by repeating back what they said, helping them come up with solutions, and being honest with them.
Transparency - Show that you are not hiding anything by being open about what is going on - do you have a delay with a project? Explain why and what you are doing to work through it. Is there bad news to deliver? Share it with the individuals it affects the most first, so that they can process it and ask questions.
Relationships - A friendly relationship with your coworkers and clients builds trust and makes working together so much more enjoyable.
What do you find most interesting/rewarding about your work? What’s the most challenging?
The most interesting part of my work is the people I work with. I love getting to know people, figuring out what makes them tick, and tailoring my approach with them so that I can truly help them. The most challenging part is trying to fit everything I want and need to do into my day. It is frustrating when you know what you want to do but can’t find the time to put towards it.
What is your proudest professional accomplishment?
I’m going to cheat and say two. First was when I led the creation of a new offering at Runkeeper that enabled us to natively bring sponsors into the app, which created cool experiences for our users and opened up a new revenue line. We weren’t sure what we were doing, but the team was amazing and we figured it out. Second has been building the Project Management team at Paperless Parts. Everyone at this company is collaborative and supportive and I’m so glad I started here in May.
Are you involved with any professional organizations outside of the company? Volunteer work?
I volunteer in various organizations in my community in Vermont.
I am also a certified PMP - Project Management Professional.
Q&A
What do you enjoy doing in your free time?
I love being outside. Hiking, running, swimming, paddling, skiing, back country skiing, snowshoeing are all on my list throughout the year. I also am an ameateur potter and am part of a cool studio near my home in Vermont.
How do you manage stress?
In general I use exercise to proactively keep stress at bay and believe that a walk or a workout can abate anxiety and stress. A glass of wine can help too.
How many cups of coffee do you have in a day?
I drink decaf iced coffee. I made a point to not become dependent on caffeine when I was in college, then I carried that through when I started working. It started as being able to deal with an apocalypse or something like that and eventually I just realized that I get anxiety from it and can’t sleep that night.
Any book or podcast recommendations?
Podcasts: I listen to Wall Street Journal’s What’s News every morning while I’m getting ready for the day. Stuff You Should Know is one of the original podcasts (I think they may have been in the first 100?) - so funny and I’ve learned a lot from them.
Other favorites: Criminal, This is Love, Noble Blood, How I Built This, Freakonomics
Books: I’m a nerd for historical fiction. In the Heart of the Sea is possibly my favorite and just recently read The Hour of the Witch and The Rose Code, which were both fantastic. I also love drama/mysteries - I more recently enjoyed The 7 1/2 Deaths of Evelyn Hardcastle, Cloud Cuckoo Land, and The Bone Clocks.
What advice do you have for recent college graduates?
Know that most people are happy to help you; don’t be afraid to reach out to people on LinkedIn / through your network to learn about their experiences and network with them. When you do meet to network, make it easy for them and come with questions so that they don’t have to drive the conversation.
WayneandGarth - I once went as Wayne and Garth from Wayne’s World with my dog Bear - people loved it and I got stopped in the street all over Boston.
HikingwithBearandRhonda - As I mentioned, I love hiking and took this photo last Fall with my dogs Bear and Rhonda.
PaperlessPartsHat - I rocked my Paperless Parts hat on a hike up Mount Washington this Summer - this is us crossing over the Cog Railway track.
